Truth or Dare?
by ContestShipper
Summary: Ash, Misty, Drew and May decide to spend a week together while May's Parents are out of town. When a game is introduced into the mix, what will happen? Contestshipping and Pokeshipping.
1. Chapter 1

**Hey guy I'm back xD  
><strong>**I'm so sorry for the delay in IDWY, I have been having writers block and I am currrently overloaded with school work, but this is a little thing I did for a contest.(Which I didn't finish on time of course)**

**So I hope you enjoy.**

_**Disclaimer: Callie does not own Pokemon or any of it's affiliates, if she did, she wouldn't be wasting her time in school right now.**_

"Hey you guys! I have to housesit this week cause the 'rents are going out of town with Max. Yall wanna come and hang out? It will be boring if I'm alone." May looked over to three of her friends.

Ash was trying to sleep when Misty bopped him on the head to get his attention. "Hey what was that for?"

"May's asking if we want to come over tonight and spend the week with her. So do you wanna come?" Misty turned and looked over at May. "I'm game. I have nothing to do anyways." She gave her a thumbs up and then looked over at Drew who had still not answered.

"I can come as well. My mom is going to visit a friend in Celadon and is going to be gone all week," replied Ash who was still rubbing his head from where Misty hit him.

"Awesome! I was really worried about being alone." Then she turned her attention to Drew. "So what about you Drew? Can you come?" May walked over towards him as she spoke. He was leaning against a desk and she leaned against the one across from him.

"Hmph, why would I want to spend a week with you loser?" A smirk spread across his face. He loved teasing her.

"Hey!" She smacked his arm playfully. "I'm no loser mister arrogance!"

"Hey, hey, I kid haha." He held his hands up in defeat; a smirk was still present on his face though. "You're gonna owe me though."

May squinted her eyes at his last statement. "Fine. . .but nothing too horrible." She waved an accusing finger at him. Normally seniors would want to go all out on dares, but not May. She never liked doing anything too extreme. She was already on edge because Halloween was next Sunday and that was not her favorite holiday.

"Alright, it's settled then! We'll come over tonight about 8 'kay?" Misty glanced between the three students.

"Yea that sounds fine to me. We can crash at your place right?" Asked Ash.

"Mmmhmm that's perfectly fine." She had already gone and picked up snacks and stuff for tonight along with a few movies cause she figured they would say yes.

"Ok, we'll see you tonight!" Misty grabbed her bag and walked out of the classroom with Ash not far behind. May then turned to face Drew. She noticed that the classroom was empty, leaving just the two of them.

"So. . .what is it that I'm going to have to do?" She leaned against the desk again crossing her arms across her chest. Drew walked over towards her, the smirk from earlier replaced with a soft smile. A light blush coated his face as he spoke.

"I was wondering if you would like to go with me to that Halloween Party that Oak is hosting next Sunday." May felt her face darken. Out of all the possible scenarios going through her head, this wasn't one of them.

"Uh Umm, su-sure." She wasn't sure why she was so nervous. Yea, her and Drew were close friends and she felt a little more about him, but it was just a party. No reason to freak out.

"Alright." A slight smirk tugged at the edge of his mouth. "It's a date then." Drew looked at her face waiting to see her reaction.

"Y-yea hehe." Her face had darkened to match her bandanna. "I-I gotta go get ready for t-tonight." She quickly stood up and grabbed her bag. "See ya later D-Drew." And with that she rushed out the door.

"Heh, she is so shy." He casually grabbed his belonging and went out to his truck. This week was too be full of surprises.

_Ding Dong Ding Dong Ding Dong_

"I'm coming!" shouted May from the kitchen. She opened the front door and saw Misty, Ash, and Drew standing on her porch. "A little impatient eh Misty? Hehe"

"Hey I'm just ready to get this show on the road! Oh and I brought us some snacks and other things." She held up a few bags that she was carrying. As everyone walked in May glanced quickly at Drew, still slightly on edge from the incident earlier. Drew noticed her looking at him and smirked. Part of him wished she would just relax; the other part still thought it was cute when she was flustered.

The four of them entered the living room which already had snacks and movies piled up. Ash was already stuffing his face with the oreo truffles when Misty popped in a movie. "Let's get it started!" Misty plopped onto the couch next to Ash and stole the truffle he was about to devour. May lay across the adjacent couch, stretching out and getting comfortable while Drew decided to take the armchair.

The watched several movies back to back not paying any attention to what time it was. After they finished Disturbia, May yawned and glanced at the clock. "Gosh it's 4 am!" she exclaimed. She looked over at the other three and noticed that Ash had fallen asleep in a bowl of popcorn, Misty was looking through the pile of movies, and Drew seemed to be bored out of his mind.

"Really?" Misty looked up at the clock. "Wow it doesn't seem like it."

"Can we do something else? These movies aren't even that great," complained Drew. He crossed his arms. Drew's complaining woke Ash up.

"Wha*yawn* is going on?" He picked up his head and looked at Misty. Some popcorn stuck to his face and his hat had fallen to the floor.

"Drew here is bored." Misty spoke nonchalantly.

"Well it_ is_ 4 am," said May. She stood up and stretched. "Let's call it a night. We have a full week to do things since we don't have school this week. Besides . . . we don't want to do everything in one night."

"Finally you say something smart," Drew replied with a smirk but it was interrupted with an obnoxious yawn from the greenette. May shot him a look but yawned as well. She walked over to the hall closet and got everyone a blanket and some pillows and returned within a few minutes to pass them out to everyone.

"We can just crash in here tonight. We can figure out sleeping arrangements tomorrow." She curled back up on the couch with her red and yellow comforter and watched everyone else get settled in. "Good night."

"Good night." The other three echoed.

**I do need to edit this because it is kinda rushed. But I wanted to give yall something for being awesome and following me. (Also I am still working on IDWY so no worries ^^)**


	2. Chapter 2

**Yay another chapter :D**

**I want to thak everybody for the reviews so far. it makes me so happy to log on and find a new one :D  
>(Also almost nobody has commented on it on dA and it makes me feel a little sad ;-;)<strong>

**Sorry this is so short though, but it's just a little fluffy chapter, full of Contestshipping ^^**

**Disclaimer: _**Callie does not own Pokemon or any of it's affiliates, if she did, she wouldn't be using a pair of crappy headphones right now.**_**

Drew was the first to wake up the next morning. The clock read 11:38, and he wasglad it was a Saturday. He looked over at the other three and had to stifle a laugh. Misty and Ash were tangled together in their blankets, curled up against one another. He shook his head, baffled at how they still hadn't gotten together. Then he looked over at May.

She was sprawled out on the couch with the blanket wrapped tightly around her. Her legs and lower body were on the couch while her upper body was lying on the floor. Drew had no idea how she had managed to end up like that, little did he know her dreams that night had mainly revolved around him.

He got up and walked towards the kitchen, figuring he should make some breakfast for the four of them. As he passed the couch May lay on, he froze. She shifted slightly, causing her to fall off the couch even more and he her heard utter a few words. "Drew . . . don't . . . go . . ." He was taken aback slightly. He knew that she was still sleeping but, even if he was only going to the kitchen, he felt that he should stay. Drew sat down on the floor next to her. He gently picked her head up off the hardwood floor and set it in his lap. She was mostly on the floor now and he wanted her to be comfortable. At his touch she moved closer, unconsciously wrapping her arms around his waist. Drew felt a light blush cross his face as she did so.

Misty began to wake up as she heard Drew going to the kitchen. She opened her eyes slightly and saw what her situation was and a blush fell across her face, but then she looked over to way Drew was. She watched the little scene unfold before her and an idea came to mind. A cat like grin spread across her face and she gently nudged Ash. "Hey sleepyhead wake up." He didn't move. "Come on wake up!" She pushed him slightly but it was enough to send him to the floor with a thud.

"Owww. . .What was that for?" He began to rub where his head had hit the floor.

"I was trying to wake you up."

Drew had started caressing her hair, letting the brunette locks move through his fingers when his head snapped up, a blush slightly forming on his face. When Ash crashed to the floor he had startled Drew but May was still sleeping. Nothing seemed to be able to wake her up.

"Well you could do it more gently," Ash added as he stood up. His stomach growled and he quickly decided to go to the kitchen for some breakfast, paying no mind to Drew and May. Ash never paid attention when food was needed. Misty however, casted a sly grin in Drew's direction before she got up to join Ash in the kitchen.

Drew shifted uncomfortably when Misty looked at him. He could tell she was up to something. The red head scared him whenever she had a plan, but he had other things to deal with at the moment. He looked down at the brunette wrapped around his waist, still sleeping away, but Drew decided it was time she woke up.

_Poke_

Nothing.

_Poke Poke_

"May. . .wake up."

Nothing.

"May get off of me." Drew tried shaking her shoulders but it still didn't work. He then eyed a leftover bowl of popcorn and got an idea. He reached over and grabbed the bowl and held it under her nose. May could never resist food so Drew was positive this would work.

_Sniff Sniff_

"Mhmm . . . Five. .more . . .minutes mom. . ." Her grip tightened as if she was clutching her pillow.

"Ummm, May? I'm not your mom." At his words, May's eyes shot open, full of alarm and shock.

"Drew!" She noticed that she was lying in lap, arms around his waist, and immediately began to blush. "Wh-What is going on!" She detached herself and moved away slightly, feeling completely embarrassed.

"Well. . .ummm. . ." Drew wasn't quite sure what to say. He could exactly say 'well I was going to make breakfast, but then you told me not to leave you so I decided to stay since I like you a lot an next thing I know you are wrapped around my waist.' It was at that time that Misty walked in again. She leaned against the doorframe between the kitchen and living room glancing at the two with a cat like grin.

"Come on you lovebirds. Breakfast is ready." As she spoke, May and Drew both began to blush. Misty just laughed and walked back into the kitchen as the two began to blush heavily and joined the others in the kitchen.

**And there we have it ^^**

**I already have the next few chapters written so I'll probably post them up about every 2 or 3 days.**

**Don't forget to Read and Review :D**


	3. Chapter 3

**Woo it's chapter 3!**

**First off, I want to thank everyone how has reviewed, Favorited, heck even read this thing. It makes me so happy that yall like my work and it makes me want to hurry up and finish the next few chapters ^^**

**Next, I will be having exams next week so I will try to upload a chapter by then. I only have up to chapter 4 written so it may take me a bit longer. Now on to the story! :D**

**_**Disclaimer: Callie does not own Pokemon or any of it's affiliates, if she did, she wouldn't be having to worry about exams next week.**_**

Breakfast didn't take long for the four of them and soon enough May began to clean up the dishes. That's when Misty began to speak.

"So. . .I have found a way to keep us entertained throughout the week. This way we won't ever be bored." She placed her elbows on the tabled and laced her fingers together.

Drew lifted an eyebrow as he shifted his gaze from his empty plate to the red head in front if him. "What's your idea?" May turned and looked as well. She didn't like Misty's tone and wondered what could be going through that girl's head. A cat like grin spread across Misty's face as the two looked at her questionably.

"Well. . .how about we play a little game of truth or dare, except slightly altered?" This piqued Drew's interest even more as well as May's. This would definitely be interesting.

"What would be the rules?," questioned May.

"We will be split into two teams. Me and Ash and you and Drew." She pulled her elbows off the table and stood up. "Each team will pick either truth or dare, the 'truth' and 'dare' have already been predetermined by our amazing friend Dawn." Misty held up her goldeen print Iphone. "I have no idea what they are so I didn't rig this thing. Jussayin." She put her phone back her in her pocket.

May puffed up her cheeks at the mentioning of her teammate, not liking the results.

"Why am I stuck with Drew? He's a horrible person to have as a teammate!" Her embarrassment from earlier had subsided and now she had her competitive edge on. In her eyes Drew would drag her down. At the comment, Drew cast her a look mixed with anger and hurt but it went unnoticed by May. Misty however saw it and knew this could work out very well.

"It's set up that way because of the challenge." At that moment the computer monitor in the kitchen flickered to life, revealing a confused Dawn.

"Hello? Can yall hear me?" She continued making funny faces, oblivious that the four of them could see what she was doing.

"Hey Dawn." Chorused the four.

"Perfect timing!" Misty gave her a thumbs up. "Are you ready to give them a debriefing?"

"Of course!" Her smile brightened. "Ok everyone. The challenge is not to fight with your partner for a week. That is why you are paired up the way you are." A sly smile crossed her face as she held up two envelopes. One read 'Truth' and one read 'Dare'. "Each pair will pick an envelope. Only one will have truth or dare. Both teams can't be the same." Dawn paused for a minute. "Yall follow me so far?"

May nodded her head as she began to speak. "How will we determine who gets what?"

"And exactly what counts as fighting?" Questioned Drew.

"We will flip a coin," answered Misty, pulling out a quarter in the process.

"And anything counts. From throwing punches to calling each other names. All in all, you have to act civil towards each other." May and Drew groaned as she finished speaking.

"I don't like this anymore. . ." May narrowed her eyes.

"For once we agree," commented Drew.

"Come on this will be fun," Ash encouraged. He had finally finished stuffing his face to comment. The five were silent for a moment when Drew finally spoke up.

"I'm in. What harm could a little game do?" He shrugged his shoulders. It would be interesting, he knew that.

"Guess I'll do it too then," replied May. She didn't want to be left out of the fun.

"Alright!" Spoke Dawn. "Now just because Misty helped set this up doesn't mean I'll go easy on her. I'll be available 24/7 in case yall need any clarification or something like that."

"Ok. So can we pick the envelopes now?" May was getting impatient now that she was going to play.

"Yup." Misty held up the coin. "Heads or Tails?"

"Tails!" Blurted out Drew. He always had luck with calling tails and besides, he wasn't mainstream.

"Ok," she flipped the coin into the air and caught it in her right hand, flipping it over on the back of her left hand. "It's. . .Heads!"

"Why did you call tails? Everyone knows you always call heads!"

"Well I'm not everyone and I always call tails!" Drew retorted.

"Guys, guys chill! This only helps decide the envelopes, it's not like yall lost or anything . . . but that would be considered and argument . . . jussayin," spoke Dawn. A grin crossed her face as she began to take an interest in her nails, hoping to rile them up a bit.

"Hmph," May blew up her bangs, "well I don't really care what happens next since Drew is apparently the boss around here." With that, she stomped off to her room.

"Girls . . ." sighed Drew.

"Psh whatever Drew. If yall keep at it, you'll lose within the hour," spoke Misty. Then she turned to face the monitor. "Since we won, I would like to pick truth Dawn."

"Ok Misty!" She grabbed the truth envelope and wrote 'Ash & Misty'. Then grabbed the dare envelope. "That means that you and May will have dare Drew."

"Ok," he mumbled. He didn't want to lose because he knew it would be his fault, and he didn't want to find out what was in the envelope.

**\o/ The game has begun. What do yall think is going to happen? And what do you think is in the envelopes? ;D**

**This was Halloween inspired so think along those lines. Who ever gets the closest will get something. . .hmmm maybe a one-shot or a drawing :D **


End file.
